8 min read · USVI Term Charters · Updated Jun 8, 2026
People often ask what a week aboard actually looks like. Not the brochure version — the real one. Here is an honest walk-through of a typical USVI term charter aboard Stella Blue, from the moment you step on the dock to the morning you head back to the airport.
Day of arrival
Most guests fly into St. Thomas (STT) and meet us at the dock in the late afternoon. You're greeted with a cold drink, shown to your cabin, and given a short walk-through of the boat. There's no rush — the first night is usually a quiet anchorage close to St. John, dinner aboard, and an early bed after a travel day.
Mornings
Coffee is up before you are. Breakfast is whenever you'd like it — fresh fruit, eggs cooked the way you want them, something baked. Most mornings start with a swim off the back of the boat before we sail to the next spot.
On the move
Sailing legs between anchorages are typically one to two hours. You can help trim a line, take the wheel, or sit on the bow with a book. There's no expectation either way. The catamaran is stable and quiet under sail, which makes the passages part of the vacation rather than something to endure.
Afternoons
Snorkeling at a reef, paddleboarding around a quiet cay, a beach landing for a walk, or an anchorage with a famous floating bar. The captain plans around weather and what you've said you want — more reef time, more beach time, more sail time, less of any of it.
Evenings
Dinner aboard is the centerpiece of most evenings: fresh seafood, grilled mains, bright sides, dessert. Some nights we anchor near a dinghy-up restaurant if you'd rather go ashore. After dinner: stars, a nightcap, and the kind of quiet you can't buy on land.
The last morning
We aim to have you back to the dock in time for an early-afternoon flight. Most guests describe the disembark as the only difficult part of the week.
Frequently asked
Common questions from guests
What airport do I fly into?
St. Thomas (STT, Cyril E. King Airport) is the standard arrival point. Most guests are aboard within an hour of clearing baggage claim.
Do I need sailing experience?
No. The captain handles the boat. Guests who want to help trim a line or take the wheel are welcome to; guests who'd rather sit on the bow with a book are equally welcome.
How long are the sailing legs?
Most legs between anchorages run one to two hours. The catamaran is stable and quiet under sail, so passages feel like part of the vacation rather than something to endure.
Do we ever go ashore?
Yes — beach landings, dinghy-up restaurants, and short island walks are all on the menu. The mix of ashore time and aboard time bends to what you want.
Keep reading
USVI Term Charters
What Is a Caribbean Term Charter?
A plain-English guide to multi-night, fully-crewed yacht charters in the Caribbean — and why couples and small groups love them.
Virgin Islands Itineraries
A Sample St. John and St. Thomas Sailing Itinerary
Christmas Cove, Pizza Pi, the starfish flats, Lime Out, and the sunset anchorages we love most.
Charter Planning Tips
What to Pack for a USVI Sailing Charter
Soft-sided bags, reef-safe sunscreen, light layers — and a few surprises that always come in handy onboard.
